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Travel from US (ORD) to Canary Islands

Hello, in May 2016 we are travelling from Chicago (O'Hare) through Madrid and on to Las Palmas Gran Canaria. I would like to know more about Immigration and Customs. On the way, do we "clear" immigration in Madrid and our checked bags go through to the island or do we collect our bags in Madrid and re-check? More importantly for the return we leave the island around 6:30pm and arrive Madrid around 10:30pm where I have booked an airport hotel. Will we be reunited with our checked baggage in Madrid that evening or will the bags be checked through to Chicago, requiring us to carry on overnight stay bags? (Sorry, I have travelled internationally before but there was never an overnight stay involved)

When you travel on "one ticket", i.e. same airline or codeshare flights, it's the norm that your luggage will be checked through to your final destination. Same for airlines with interline agreements.

But if you have, for example, a long-haul ticket ORD-MAD with Iberia or American and connect to a low-cost carrier like Ryanair to go from MAD to LPA you will have to claim and re-check your bags in MAD.

Going back from LPA to ORD, there can be several scenarios. In the end, only your airline(s) will be able to tell you which one will apply.

1) As there is an overnight stay involved, you need to claim bags in MAD and check them in again next day.
2) Even if 1) applies, some airlines at some airports have dedicated bag drop desks (landside) in the evening hours to check in bags for next day departures.
3) Even though an overnight stay is involved, your airline may check through the bags (and keep them overnight in MAD)
4) If 3) applies but you want your bags you can inquire if you can short check them at LPA to MAD. Meaning that you will be able to collect them and proceed as in 1)

This depends on how your tickets where purchased, the crucial information you have not provided. You can collect, but if you are booked on one ticket, you don't want to collect unless the layover is very very long.

>>> Will we be reunited with our checked baggage in Madrid that evening or will the bags be checked through to Chicago, requiring us to carry on overnight stay bags?

Again the same lacking ticketing information. If on one ticket, YOU tell the counter at LPA how far you want you luggage checked. There are trade offs. So you are arriving in MAD at 10:30pm. Having to retrieve your luggage delays getting to your hotel. It also requires you to get to the counter earlier next day than if you could just walk to the security with your boarding pass. On the other hand, I don't like my luggage left for many hours in the luggage handling area. My luggage were often rummaged through when they were left in the luggage handling area for many hours.

There is nothing like "immigration" in the USA in Europe. When you leave the intercontinental plane in Madrid, there is just a passport control. Quick and easy, no forms, no questions.

If you have a connecting flight, you will stay within the international area of the airport, so there is no customs.

Normally, your baggage will be checked through to your final destination. You will go through customs just before you leave your final airport (as said, no big thing - again no forms, no questions, you just go through the green channel). Chances are extremely low that you baggage will be checked unless you have illegal drugs in your baggage.

For your return flight, you have the choice how your baggage is treated. At the check-in counter in Las Palmas you can ask to get it back in Madrid, otherwise it will be checked through to Chicago (if I were you it would choose the latter option and put my night things in a small carry-on).

You'll be arriving at Terminal 4A and have to clear passport control in Terminal 4. What happens after that depends on which connecting flight your taking. About half of the flights to Gran Canaria (LPA) depart from T4, another group from T2 and three from T3.